Process of producing camphene.



CHARLES GLASER, OF BALTIMORE, MARYLAND.

PROCESS or ritonuonvo CAMPI-IENE.

Specification of Letters Patent.

Patented June 8, 1909.

Application filed December 11, 1905. Serial No, 291,380.

material belongs to the borneol series,-

having a formula as follows :G,,H,,HC1.

Heretoforeit has been customary to prepare camphene by the saponification of bornyl-chlorid by means of-causti alkalies,lime, anilin, acetates of alkalies, and other similar substances; it being believed that the presence of some basic substance was necessary to remove the HCl group from the hydro-carbon.

I have discovered that if bornyl-chlorid or as the substance is more properly called bornyl-chlorid, be distilled at a temperature of from 180 to 210 0., a dissociation takes place resulting in the formation of hydrochloric acid and camphene, two separate stablecompou'nds, which may be separated by passing the gases through a still in which the camphene may be condensed while the hydrochloric acid will not only not be-con-.

densed but will not reunite with the camphene' to reform bornyl chlorid, but may be led off and preserved for future use, while the camphene if redistilled, at 157--5 to 158-5 C. may be purified and obtained'in crystalline form practically pure.

Pinene-hydro-chlorid boils at 210 C.,

dipentcne at 1745 0., camphene at 157-5 to 158-5 C.

When distillation is begun the hydrochloric acid begins to go off at a temperature of about 1575 C. and at" the same time some camphene is formed. As the temperature rises the point must be passed at which dipentene will be formed by the dissociation of the hydrochloric acid gas.

It is the purpose of this process to produce a cam hene and not dipentene.

I ave foundthat if the bornyl-chlo'rid is heated up rapidly to a temperaturcof 180 to 190 0., andthc distillate whether of camhene, dipentmic or bornyl-chlorid\ is re- Suxedor returned to the original vessel and the heating continued, that as the quantity of camphene increases the temperature at which the rearrangement of molecules takes place with the formation of HClwill become less, and finally, after this distillation and return of the distillate has been carried on for a period of an hour or longer, if the dis-.

tillate instead of being returned to the still is collected and separated, it will be found to contain a high per cent. of camphene. About 70% has been obtained. If this distillate be redistilled at a temperature of 157--5 to 158-5 (3., pure camphene may be recovered.

I have found that heat alone is necessary to produce camphene and hydrochloric acid by the decomposition of bornyl-chlorid, but this action may be accelerated or prevented by the presence of various substances. Sharp sand or any insoluble inert material with sharp edges Will to some extent assist the action,so1ne metals and metallic compounds such as copper or a copper compound will greatly assist the action, while iron and zinc will almost entirely prevent the formation of camphene but produce. substances quite different from can'iphcne. The action of sand or copper ora copper compound appears to be catalytic. The presence of the catalytic agent not only assists the formation of camphene but. also retards and in great measure prevents the formation of dipentene.

Having thus described my invention, what I claim and desire to secure by Letters Patent is:

1. The production of camphene from bornyl-chlorid by the distillation of that substance at a temperature between 180. and 210 C. and fora time refluxing the distillate, then separating the distillate and collooting it.

2. The production of camphene from bornyl-chlorid by the distillation of that substance at a temperature between 180 and 210 C. and for a period of time refluxing the distillate while allowing the vapor of hydrochloric acid to escape, then condensing and separating the distillate.

3. The process for making camphene which consists of subjecting bornyl-chlorid to distillation under conditions which will permit the escape of HCl and the collection of the camphene as a distillate.

4- The process of producing camphene from bornyl-chlorid which consists of heating this substance to a temperature of 180 to 210 degrees C. producing a separation of the HCl, and collecting the camphene as a distillate; i

5. The production of camphene from bornyl-chlorid which consists of heating that substance to a temperature of from 180 to 210 0., when hydro-chloric acid and camahene will be produced by separation, conilensing the camphcne, and passing off the 'hydro-chloric acid gas.

6. The production of camphene from bornyl-chlorid which consists of heating that substanceto a temperature of from 180? to 210 0. when hydro-chloric acid and camphene will be produced by dissociation of the pinene-hydro-chlorid, condensip the camphene, and then redistilling th' cam ph'ene at a temperature of 157-5 to'1585 C.

7. The method of producing camphene which consists of heatmgbornyl-chlorid in the presence of a catalytic agent.

8. Themethod of producing'camphene which consists of'distilling bornyl-chlorid in the presence of substance containing c0 per.

9. The method of producing camp liene which consists of distilling bornyl-chlorid at a temperature of from 180 to 210 O.-, re turning the distillate to the still for a period of time, while passing off the separated hydro-chloric acid, and then separatnig the distillate and subsequently redlstilling the distillate at a temperature of from 1575 acid, and then separatlng the dlstillatc and subsequently redistilling the distillate-at a temperature of from 157 5 to 1585, when practically pure camphene may be recovered. Si ned by me at Baltimore city and State of L aryland this 5 day 0 December 1905.

CHARL 4 S GLASER.

' Witnesses:

THEODORE E. STBAUS,-

FLORENCE BARRETT. 

